This invention related to the production of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) at commercial scale from the reaction of 1,1,1,3,3-pentachloropropane (HCC-240fa) and HF. HCFC-1233zd is a low global warming compound that has applications as a replacement for high global warming materials, for example in foam blowing and aerosol propellant applications.
The term HCFC-1233 is used herein to refer to all trifluoro, monochloro propenes, namely olefin compounds having the general formula C3H2ClF3. The term HCFC-1233zd is used herein generically to refer to 1,1,1-trifluo-3, chloro-propene, independent of whether it is the cis form or the trans form. The terms “cis HCFC-1233zd” and “trans HCFC-1233zd” are used herein to describe the cis- and trans-forms of 1,1,1-trifluo-3-chlororopropene, respectively. The term “HCFC-1233zd” therefore includes within its scope cis HCFC-1233zd, trans HCFC-1233zd, and all combinations and mixtures of these. The designation “1233zd” is also used herein for these compounds.
U.S. Pat. No. 6,844,475 teaches a process for producing 1233zd from 240fa at low pressure and at temperatures lower than 150° C. The disclosure of this patent is hereby incorporated herein by reference.
U.S. Pat. No. 6,362,383 teaches a process for preparing 1,1,1,3,3-pentafluoro-propane (HFC-245fa) by (1) a first reaction step in which 1,1,1,3,3-pentachloropropane (HCC-240fa) is reacted with hydrogen fluoride in the liquid phase in the presence of a first hydrofluorination catalyst under conditions that are suitable for obtaining a mixture of reaction products comprising 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) in substantial amount, and (2) a second reaction step in which the 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) obtained from the first step is reacted with hydrogen fluoride in the liquid phase in the presence of a second hydrofluorination catalyst, and preferably while hydrogen chloride is continuously fed in, in order to obtain 1,1,1,3,3-pentafluoro-propane (HFC-245fa). The disclosure of this patent is hereby incorporated herein by reference.